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WO2006105862A1 - N-[pyrimidin-2-yl-methyl]carboxamides substitues et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale - Google Patents

N-[pyrimidin-2-yl-methyl]carboxamides substitues et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale Download PDF

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Publication number
WO2006105862A1
WO2006105862A1 PCT/EP2006/002508 EP2006002508W WO2006105862A1 WO 2006105862 A1 WO2006105862 A1 WO 2006105862A1 EP 2006002508 W EP2006002508 W EP 2006002508W WO 2006105862 A1 WO2006105862 A1 WO 2006105862A1
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WIPO (PCT)
Prior art keywords
alkyl
hydrogen
cycloalkyl
alkoxy
halogen
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PCT/EP2006/002508
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German (de)
English (en)
Inventor
Michael Gerhard Hoffmann
Klaus Haaf
Hendrik Helmke
Lothar Willms
Thomas Auler
Martin Hills
Heinz Kehne
Dieter Feucht
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to AU2006231020A priority Critical patent/AU2006231020A1/en
Priority to CA002603169A priority patent/CA2603169A1/fr
Priority to JP2008503402A priority patent/JP2008534536A/ja
Priority to MX2007012243A priority patent/MX2007012243A/es
Priority to EP06707605A priority patent/EP1871746A1/fr
Priority to BRPI0609796-0A priority patent/BRPI0609796A2/pt
Publication of WO2006105862A1 publication Critical patent/WO2006105862A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel, herbicidally active N- [pyrimidin-2-ylmethyl] carboxamide derivatives, processes for their preparation and their use as herbicides and plant growth regulators, in particular for the selective control of weeds and weeds in crops of useful plants.
  • the object of the present invention is to provide herbicidally active compounds with improved herbicidal properties and improved compatibility with crop plants compared to the compounds known from the prior art.
  • R 1 and R 2 independently of one another are hydrogen, halogen, cyano, amino, isocyano, hydroxyl, nitro, COOR 5 , COR 5 , CH 2 OH, CH 2 SH, CH 2 NH 2 , (C 1 -C 4 ) -alkyl , halo (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) alkoxy, halo (C r C 4) alkoxy, (C 1 -C 2) - (2 C r C) alkyl alkoxy, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C 3 - C 4) alkenyloxy, (C 3 -C 4) alkynyloxy , (C 1 -C 2) -alkylthio- (C 1 -C 2) alkyl, S (O) n R 6, (-C 2) -alky
  • R 3 is hydrogen, (C r C4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, benzyl, COOR 5, COR 4 or S (O) n R 6;
  • R 4 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, substituted by one or two methyl groups (C 3 -C 6) - cycloalkyl, (Ci-C 2) alkoxy (CrC 2) alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 2) alkyl, halo (CrC 6 ) -alkyl or halo (C 3 -C 6 ) -cycloalkyl;
  • R 5 is hydrogen or (C r C 4 ) alkyl
  • R 6 is hydrogen, (CrC 4) alkyl or HaIogen- (C r C4) alkyl;
  • A is a radical from the group comprising the substituents A1 to A8
  • R 8 is hydrogen, halogen, cyano, isocyano, nitro, (Ci-C 4) alkyl, halo (C- ⁇ -C 4) alkyl, (Ci-C 4) alkoxy, halo (Ci-C 4 ) -alkoxy, halo (C 1 -C 4 ) -alkylthio, (C 3 -C 6 ) -cycloalkyl, halo (C 3 -C 6 ) -cycloalkyl, SF 5 , S (O) n R 6 , (C 2 -C 4 ) -alkenyl or (C 2 -C 4 ) -alkynyl;
  • R 9 is hydrogen, halogen, cyano, isocyano, nitro, (CiC 4) alkyl, halo (C r C 4) alkyl, (CrC 4) alkoxy, halo (CiC 4) alkoxy, ( C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or S (O) n R 6 ;
  • R 1U represents (C 1 -C 4 ) -alkyl
  • XA, X v2 independently of one another denote hydrogen or (C 1 -C 4 ) -alkyl
  • n 0, 1 or 2.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl.
  • Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • the multiple bond may be in any position of the radical.
  • the radical propynyl may be 1-propynyl or 2-propynyl.
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods.
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention also relates to all stereoisomers and mixtures thereof which include but are not specifically defined by the general formula (I).
  • R 1 and R 2 independently of one another are hydrogen, halogen, cyano,
  • R 3 is hydrogen, (C r C 2 ) alkyl, benzyl or COR 4 ;
  • R 4 is hydrogen, (C r C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, substituted by a methyl group (C3 -C 6 ) -cycloalkyl, (Cr C 2) alkoxy (Ci-C 2) alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 2) alkyl, halo (C r C 4) - alkyl or halo (C 3 -C 6 ) cycloalkyl;
  • R 5 is hydrogen or (C r C 4 ) alkyl
  • R 6 is hydrogen, (C r C 2) alkyl or halo (CrC 2) alkyl;
  • A is a radical from the group comprising the substituents A1 to A8;
  • R 8 is hydrogen, halogen, cyano, (Ci-C 2) alkyl, halo (C r C 2) alkyl, (C 1 -C 2) (Ci-C 2) alkoxy, alkoxy, halogen Halogen (C 1 -C 2 ) -alkylthio, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -C 6 ) -cycloalkyl, S (O) n R 6 , (C 2 -C 4 ) -alkeny! or (C 2 -C 4 ) alkynyl;
  • R 9 is hydrogen, halogen, cyano, nitro, (C- ⁇ -C 2) alkyl, HaIOgBn- (C 1 -C 2) - alkyl, (CrC 2) alkoxy, halo (Ci-C 2) - alkoxy, (C 2 -C 2 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl or S (O) n R 6 ;
  • R 10 is methyl or ethyl
  • X 1 , X 2 independently represent hydrogen or methyl
  • n O, 1 or 2.
  • R 1 and R 2 are each independently hydrogen, halogen, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, ethoxymethyl, methoxymethyl, thiomethyl, methylsulfonyl, or R 3 1 and R 2 together form the group (CH 2 ) 3 ;
  • R 3 is hydrogen, methyl, ethyl or COR 4 ;
  • R 4 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, cyclopropyl substituted by a methyl group, (CrC 2 ) - alkoxy- (Ci-C 2 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 2 ) -alkyl I halogen- (Ci-C 4 ) -alkyl or halogen- (C- 3 - C 6 ) cycloalkyl;
  • R 5 is hydrogen or (C 1 -C 4 ) -alkyl
  • R 6 is hydrogen, methyl or ethyl
  • A is a radical from the group comprising the substituents A1 to A6;
  • R 8 is hydrogen, halogen, cyano, methyl, ethyl, (2 Ct-C) alkyl halogen, (CrC 2) alkoxy, halomethoxy, (C 3 -C 6) cycloalkyl or S (O) n R 6 ; very particular preference is given to trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy and chlorine;
  • R 9 is hydrogen, halogen, cyano, nitro, methyl, ethyl, halo (C- ⁇ -C 2) - alkyl, (Ci-C 2) alkoxy, halomethoxy, (C 2 -C 2) alkenyl, ( C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl or S (O) n R 6 ;
  • R 10 is methyl or ethyl
  • X 1 , X 2 are hydrogen
  • n 0 or 2.
  • the compounds of the formula V can be prepared, for example, according to Scheme 4 by reduction of the corresponding 2-azidomethylpyrimidines of the formula VI with hydrogen sulphide.
  • 2-azidomethylpyrimidines of the formula VI can be synthesized, for example, directly from the corresponding 2-hydroxymethylpyrimidines of the formula VII by base-catalyzed reaction with phosphoric acid diphenyl ester azide.
  • 2-hydroxymethylpyrimidines of the formula VII are obtainable, for example, by ether cleavage of corresponding 2-methoxymethyl-pyrimidines of the formula VIII with boron trichloride.
  • the reactions listed in Scheme 4 are known to the person skilled in the art.
  • 4-methylthiopyrimidines of the formula VIII can be prepared from 4-chloropyrimidines of the formula IX by base-induced reactions with thiomethanol.
  • the chloropyrimidines of the formula IX are accessible from hydroxypyrimidines of the formula X by reactions with halogenating reagents such as thionyl chloride, phosgene, phosphorus oxychloride or phosphorus pentachloride.
  • the compounds of the formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It is usually irrelevant whether the substances are applied in the pre-sowing, pre-emergence or postemergence process. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • Harmful plants occurring under the specific culture conditions in rice such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus are also excellently controlled by the active compounds according to the invention. If the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
  • the compounds according to the invention show an excellent action against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor as well as against species of Amaranthus, Galium and Kochia.
  • the compounds of the present invention have excellent herbicidal activity against mono- and dicotyledonous weeds
  • crops of economically important crops such as e.g. Wheat, barley, rye, rice, maize, sugar beet, cotton and soybean are negligibly or not at all damaged.
  • they have excellent compatibility in corn, rice, cereals and soybean.
  • transgenic plants Due to their herbicidal properties, these compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • the compounds of the formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant, in particular soybean and maize.
  • new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be generated by genetic engineering techniques (see, eg, EP-A-0221044, EP-A-0131624).
  • genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants which are resistant to certain glufosi-type herbicides.
  • nate eg EP-A 0242236, EP-A 0 242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are transgenic crops, for example cotton, with the ability Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A 0 142 924, EP-A 0 193 259). transgenic crops with modified fatty acid composition (WO 91/13972).
  • the production of plant cells having a reduced activity of a gene product can e.g. can be achieved by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a co-suppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may in principle be plants of any plant species, ie both monocotyledonous and dicotyledonous plants.
  • the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the substances according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.
  • the compounds according to the invention can be used in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • Another object of the invention therefore also herbicidal agents containing compounds of formula (I).
  • the compounds of the formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined.
  • Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC) 1 emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, dusts (DP), capsule suspensions (EC) CS), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG) 1 ULV formulations, microcapsules and waxes , These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie", Volume 7, C.
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants), eg polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates in addition to the active ingredient except a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type (wetting agents, dispersants), eg polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates in addition to the active ingredient except
  • the herbicidal active compounds for example, in conventional apparatus such as Hammer mills, blower mills and air-jet mills finely ground and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, DMF, XyIoI or higher-boiling aromatics or hydrocarbons or mixtures of these solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, DMF, XyIoI or higher-boiling aromatics or hydrocarbons or mixtures of these solvents
  • surfactants e.g., ionic and / or nonionic type
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene sorbitan fatty acid esters.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • Emulsions e.g. Oil-in-water (EW) emulsions may be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as those described e.g. listed above for the other formulation types.
  • EW Oil-in-water
  • Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material.
  • adhesives for example polyvinyl alcohol, sodium polyacrylate or mineral oils
  • suitable active ingredients in the usual manner for the production of fertilizer granules - if desired in Mixture with fertilizers - be granulated.
  • Water-dispersible granules are usually prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I).
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • other pesticide-active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix.
  • known active compounds can be used as combination partners for the active compounds according to the invention in mixture formulations or in a tank mix, as described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and cited therein.
  • Examples of known herbicides which can be combined with the compounds of the formula (I) are the following active substances (Note: The compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name , optionally together with a common code number): acetochlor; acifluorfen; aclonifen; AKH 7088, ie methyl [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; alachlor; alloxydim; ametryn; amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurones (DPX-A8947); aziprotryn; barban; BAS 516H, ie 5-fluoro-2-
  • the formulations present in commercially available form are optionally diluted in, for example, wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable Solutions are usually no longer diluted with other inert substances before use.
  • the external conditions such as temperature, humidity, the type of herbicide used, inter alia, the required application rate of the compounds of the formula (I) varies. It can vary within wide limits, for example between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 5 and 750 g / ha, in particular between 5 and 250 g / ha.
  • reaction mixture is added to 20 ml of sodium disulphite solution (10%) and extracted four times with 15 ml of CH 2 Cl 2 .
  • Reaction mixture are 72 h at RT and then concentrated in vacuo.
  • Residue is dissolved in H 2 O, with conc. HCl to pH 5 and several times with
  • a dust is obtained by mixing 10 parts by weight of a compound of general formula (I) and 90 parts by weight of talc as an inert material and in a
  • a wettable powder easily dispersible in water is obtained by mixing 25 parts by weight of a compound of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting and dispersing agent, and grinded in a pin mill.
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the general formula (I), 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71% by weight.
  • Parts of paraffinic mineral oil (boiling range, for example, about 255 to about 277 0 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granule is obtained by
  • a water-dispersible granule is also obtained by reacting 25 parts by weight of a compound of general formula (I), 5 "2,2 1 -dinaphthylmethane-6,6'-disulphonic acid sodium,
  • Seeds of monocotyledonous and dicotyledonous weed plants are placed in sandy soil in cardboard pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders or emulsion concentrates are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha in different dosages.
  • the pots are placed in the greenhouse and kept under good growth conditions for the weeds.
  • the visual assessment of plant damage or run-on damage occurs after emergence of the test plants after a test period of 3 to 4 weeks in comparison to untreated controls. After 3 to 4 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the compounds is scored.
  • the compounds according to the invention have outstanding activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants, see Tables A to G.
  • the compounds according to the invention formulated as wettable powders or as emulsion concentrates are sprayed onto the surface of the green parts of the plant at a dosage of water of 600 to 800 l / ha in various dosages. After 3 to 4 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the compounds is scored.
  • the compounds according to the invention have outstanding activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants, see Tables H to J.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention a trait à des N-[pyrimidin-2-yl-methyl]carboxamides de formule (I). Dans cette formule générale (I), X<SUP>1</SUP> et X<SUP>2</SUP> représentent hydrogène ou méthyle, R<SUP>1</SUP> à R<SUP>4</SUP> représentent un noyau aromatique ou hétéroaromatique.
PCT/EP2006/002508 2005-04-02 2006-03-18 N-[pyrimidin-2-yl-methyl]carboxamides substitues et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale Ceased WO2006105862A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2006231020A AU2006231020A1 (en) 2005-04-02 2006-03-18 Substituted N-[pyrimidin-2-ylmethyl]carboxamides and their use as herbicides and plant growth regulators
CA002603169A CA2603169A1 (fr) 2005-04-02 2006-03-18 N-[pyrimidin-2-yl-methyl]carboxamides substitues et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale
JP2008503402A JP2008534536A (ja) 2005-04-02 2006-03-18 置換されたｎ−［ピリミジン−２−イルメチル］カルボキサミド並びにそれらの除草剤及び植物成長調節剤としての使用
MX2007012243A MX2007012243A (es) 2005-04-02 2006-03-18 N-[pirimidin-2-il-metil]carboxamidas sustituidas y su utilizacion como herbicidas y reguladores del crecimiento de las plantas.
EP06707605A EP1871746A1 (fr) 2005-04-02 2006-03-18 N-[ypyrimidin-2-yl-methyl]carboxamides substitues et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale
BRPI0609796-0A BRPI0609796A2 (pt) 2005-04-02 2006-03-18 n-[pirimidin-2-il-metil]carboxamidas substituìdas e seu uso como herbicidas e reguladores do crescimento de plantas

Applications Claiming Priority (2)

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DE102005014906A DE102005014906A1 (de) 2005-04-02 2005-04-02 Substituierte N-[Pyrimidin-2-yl-methyl]carboxamide und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE102005014906.5 2005-04-02

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US (1) US20060223708A1 (fr)
EP (1) EP1871746A1 (fr)
JP (1) JP2008534536A (fr)
CN (1) CN101151253A (fr)
AR (1) AR053196A1 (fr)
AU (1) AU2006231020A1 (fr)
BR (1) BRPI0609796A2 (fr)
CA (1) CA2603169A1 (fr)
DE (1) DE102005014906A1 (fr)
MX (1) MX2007012243A (fr)
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WO (1) WO2006105862A1 (fr)

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US8962584B2 (en) 2009-10-14 2015-02-24 Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. Compositions for controlling Varroa mites in bees
BR112012022570A2 (pt) 2010-03-08 2015-10-06 Monsato Technology Llc moléculas de polinucleotídeo para regulação de gene em plantas.
WO2013040033A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
CN103957696B (zh) 2011-09-13 2019-01-18 孟山都技术公司 用于杂草控制的方法和组合物
UA116093C2 (uk) 2011-09-13 2018-02-12 Монсанто Текнолоджи Ллс Спосіб та композиція для боротьби з бур'янами (варіанти)
US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
US10760086B2 (en) 2011-09-13 2020-09-01 Monsanto Technology Llc Methods and compositions for weed control
EP2755467B1 (fr) 2011-09-13 2017-07-19 Monsanto Technology LLC Procédés et compositions pour lutter contre les mauvaises herbes
US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
US10240161B2 (en) 2012-05-24 2019-03-26 A.B. Seeds Ltd. Compositions and methods for silencing gene expression
US10683505B2 (en) 2013-01-01 2020-06-16 Monsanto Technology Llc Methods of introducing dsRNA to plant seeds for modulating gene expression
WO2014106838A2 (fr) 2013-01-01 2014-07-10 A.B. Seeds Ltd. Procédés d'introduction d'arnds dans des graines de plante pour moduler l'expression des gènes
EP2971185A4 (fr) 2013-03-13 2017-03-08 Monsanto Technology LLC Procédés et compositions utilisables pour lutter contre les mauvaises herbes
MX2015012334A (es) 2013-03-13 2016-02-05 Monsanto Technology Llc Metodos y composiciones para el control de malezas.
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JP6668236B2 (ja) 2013-07-19 2020-03-18 モンサント テクノロジー エルエルシー Ｌｅｐｔｉｎｏｔａｒｓａ防除用組成物及びその方法
US9850496B2 (en) 2013-07-19 2017-12-26 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
AU2014341879B2 (en) 2013-11-04 2020-07-23 Greenlight Biosciences, Inc. Compositions and methods for controlling arthropod parasite and pest infestations
UA119253C2 (uk) 2013-12-10 2019-05-27 Біолоджикс, Інк. Спосіб боротьби із вірусом у кліща varroa та у бджіл
US10334848B2 (en) 2014-01-15 2019-07-02 Monsanto Technology Llc Methods and compositions for weed control using EPSPS polynucleotides
BR112016022711A2 (pt) 2014-04-01 2017-10-31 Monsanto Technology Llc composições e métodos para controle de pragas de inseto
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UA125244C2 (uk) 2014-07-29 2022-02-09 Монсанто Текнолоджі Елелсі Спосіб умертвіння або припинення росту комахи
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EP3302053B1 (fr) 2015-06-02 2021-03-17 Monsanto Technology LLC Compositions et procédés pour l'administration d'un polynucléotide dans une plante
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WO1998040379A1 (fr) * 1997-03-11 1998-09-17 E.I. Du Pont De Nemours And Company Herbicide d'heteroaryle azole

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EP1871746A1 (fr) 2008-01-02
AR053196A1 (es) 2007-04-25
BRPI0609796A2 (pt) 2010-04-27
CN101151253A (zh) 2008-03-26
MX2007012243A (es) 2007-12-07
US20060223708A1 (en) 2006-10-05
CA2603169A1 (fr) 2006-10-12
AU2006231020A1 (en) 2006-10-12
JP2008534536A (ja) 2008-08-28
DE102005014906A1 (de) 2006-10-05
TW200715965A (en) 2007-05-01

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